A Harbor Islands day is a boat out and a boat back, and the timetable decides when you leave. Ferries run from the downtown waterfront to Georges Island, roughly May to Columbus Day. Most islands have no shop and no drinking water. Castle Island is the free version that needs no boat.
Updated October 21, 2026 · refreshed weekly
Ferries leave the downtown waterfront for Georges Island, the hub, with inter-island shuttles from there to Spectacle, Peddocks and the smaller islands. The two islands most families want are both on the main ferry, which matters when you are counting connections with a tired child.
Fort Warren, a granite Civil War-era fort with dark corridors and a genuinely good ghost story, and the hub every inter-island shuttle leaves from.
Six and up, for the fort and the corridors
You came for a beach — that is Spectacle
Swimming beaches, a visitor center, gentle walking paths and the best skyline view in the harbor.
Young children, and anyone who wants one island done slowly
The forecast is hot and still — there is nowhere to get out of the sun
You carry in everything for four to six hours and carry it all out again. The harbor also runs about ten degrees colder and windier than the mainland.
Take the earliest comfortable ferry rather than the mid-morning one, and do the fort or the beach in the first two hours while everyone is fresh. Treat the second half as slow wandering.
Castle Island in South Boston gives you a granite fort and the same harbor for nothing, with no timetable attached. Despite the name it is joined to the mainland by walkways and roads.
A free 22-acre DCR park built around Fort Independence, a pentagonal five-bastioned granite fort of 1834–1851 on both the State and National Registers of Historic Places.
Free, and the Castle Island Association's tours are free too
Families who want the fort without committing to a ferry
Pleasure Bay, the M Street Beach and Carson Beach form a three-mile stretch of parkland along the shoreline, with a walkway you can walk, bike or run from Castle Island to the Kennedy Library.
Free
Buggies, scooters and anyone who wants an exit at any point
The harbor's other trips solve different problems, and every one of them is seasonal and weather-dependent.
A three-to-four-hour run out to Stellwagen Bank in open water, leaving from the same waterfront as the island ferries.
Eight- and nine-year-olds, who will remember it for years
Anyone in the family gets carsick — this is the biggest commitment on the water
The gentler version: shorter, closer to shore, and past Boston Light on Little Brewster, the oldest lighthouse station in the country.
Younger children, and anyone prone to motion sickness
Guided paddling tours around the inner harbor islands.
Older children and confident paddlers
Your child has never paddled — this is not the place to start
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Boston Harbor Islands Partnership Meeting (Boston Harbor Islands National Recreation Area) — Representatives from federal, state, city, and nonprofit agencies discuss island stewardship; public invited to provide input. All ages.
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No. Ferry service stops after Columbus Day and there is no winter option. Castle Island in South Boston is the year-round substitute: a free granite fort on the harbor, reachable by road and on foot, open whatever the season.
A lighthouse cruise. It is shorter and stays close to shore, unlike the whale watch, which is three to four hours in open water at Stellwagen Bank. Keep the whales for a year when everyone's stomach is older.
Not any more. It is connected to the mainland by both walkways and roads, so you drive or take the bus and walk straight on. That is the whole appeal: a harbor fort with no ferry, no ticket and no last boat home.